Liquid crystal composition containing polymerizable compound and liquid crystal display element using the same

Abstract

Provided are a liquid crystal composition containing, as a first component, a polymerizable compound represented by general formula (I): R 11 —S 11 -L 11 -(M 11 -L 12 ) m -M 12 -L 13 -(M 13 -L 14 ) n -Z 11   (I) and a liquid crystal display element using the liquid crystal composition.

What is claimed is: 
     
       1. A polymerizable-compound-containing liquid crystal composition comprising:
 as a first component, at least one compound selected from polymerizable compounds represented by general formula (I):
   R 11 —S 11 -L 11 -(M 11 -L 12 ) m -M 12 -L 13 -(M 13 -L 14 ) n -Z 11   (I)
 
 
 (wherein R 11  represents a group selected from groups represented by formulae (R-1) to (R-15): 
 
       
         
           
           
               
               
           
         
         S 11  represents an alkylene group having 1 to 12 carbon atoms or a single bond, where a methylene group in the alkylene group may be substituted with an oxygen atom, —COO—, —OCO—, or —OCOO— as long as oxygen atoms are not directly bonded to each other, 
         Z 11  represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a thiocyanate group, a trifluoromethoxy group, a trifluoromethyl group, a difluoromethoxy group, or an alkyl group having 1 to 12 carbon atoms where a methylene group in the alkyl group may be substituted with an oxygen atom, a sulfur atom, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, or —C≡C— as long as oxygen atoms are not directly bonded to each other, or Z 11  represents —S 12 —R 12  (where R 12  independently represents the same group as that represented by R 11 , and S 12  independently represents the same group or bond as that represented by S 11 ), 
         L 11 , L 12 , and L 14  each independently represent a single bond, —O—, —S—, —CH 2 —, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, —COO—, —OCO—, —OCOOCH 2 —, —CH 2 OCOO—, —CO—NR a —, —NR a —CO—, —SCH 2 —, —CH 2 S—, —CH═CH—COO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—OCO—, —CH═CCH 3 —COO—, —COO—CCH 3 ═CH—, —OCO—CCH 3 ═CH—, —CH═CCH 3 —OCO—, —COOC 2 H 4 —, —OCOC 2 H 4 —, —C 2 H 4 OCO—, —C 2 H 4 COO—, —OCOCH 2 —, —CH 2 COO—, —CH 2 OCO—, —COOCH 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF 2 —, —CF 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, or —C≡C— (where R a  represents an alkyl group having 1 to 4 carbon atoms), 
         L 13  represents —COOC 2 H 4 —, —OCOC 2 H 4 —, —C 2 H 4 COO—, or —C 2 H 4 COO—, 
         M 11  and M 13  each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, an indane-2,5-diyl group, a tetrahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, M 11  and M 13  may each be independently unsubstituted, or a hydrogen atom contained in any of these groups independently represented by M 11  and M 13  may be substituted with an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a halogen atom, a cyano group, or a nitro group, 
         M 12  represents a 1,4-phenylene group or a naphthalene-2,6-diyl group, M 12  may be unsubstituted, or a hydrogen atom contained in the 1,4-phenylene group or the naphthalene-2,6-diyl group may be substituted with an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a halogen atom, a cyano group, or a nitro group, m represents 0 or 1, n represents 1, 2, or 3, when n represents 2 or 3, M 13 s, the number of which is 2 or 3, may be the same or different and L 14 s, the number of which is 2 or 3, may be the same or different);
 as a second component, at least one compound represented by general formula (II):
   R 21 -M 21 -L 21 -M 22 -(L 22 -M 23 ) o -R 22   (II)
 
 
 
         (wherein R 21  and R 22  each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, one methylene group or two or more non-adjacent methylene groups in the alkyl group or the alkenyl group may each be substituted with —O— or —S—, and one or more hydrogen atoms in the alkyl group or the alkenyl group may each be substituted with a fluorine atom or a chlorine atom, 
         M 21 , M 22 , and M 23  each independently represent a group selected from the group consisting of 
         (a) a trans-1,4-cyclohexylene group (where one methylene group or two or more non-adjacent methylene groups in the trans-1,4-cyclohexylene group may each be substituted with —O— or —S—), 
         (b) a 1,4-phenylene group (where one —CH═ group or two or more non-adjacent —CH═ groups in the 1,4-phenylene group may each be substituted with a nitrogen atom), a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, and 
         (c) a 1,4-cyclohexenylene group, a 1,4-bicyclo(2.2.2)octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 
         o represents 0, 1, or 2, 
         L 21  and L 22  each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —CH═CH—, —CH═N—N═CH—, or —C≡C—, when a plurality of L 22 s is present, L 22 s may be the same or different, and when a plurality of M 23 s is present, M 23 s may be the same or different); and
 as a third component, at least one compound selected from the group consisting of compounds represented by general formulae (IIIa), (IIIb), and (IIIc): 
 
       
       
         
           
           
               
               
           
         
         (wherein R 31 , R 32 , and R 33  each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, one methylene group or two or more non-adjacent methylene groups in the alkyl group or the alkenyl group may each be substituted with —O— or —S—, and one or more hydrogen atoms in the alkyl group or the alkenyl group may each be substituted with a fluorine atom or a chlorine atom, 
         M 31 , M 32 , M 33 , M 34 , M 35 , M 36 , M 37 , and M 38  each independently represent a group selected from the groups consisting of 
         (d) a trans-1,4-cyclohexylene group (where one methylene group or two or more non-adjacent methylene groups in the trans-1,4-cyclohexylene group may each be substituted with —O— or —S—), 
         (e) a 1,4-phenylene group (where one —CH═ group or two or more non-adjacent —CH═ groups in the 1,4-phenylene group may each be substituted with —N═), a 3-fluoro-1,4-phenylene group, and a 3,5-difluoro-1,4-phenylene group, and 
         (f) a 1,4-cyclohexenylene group, a 1,4-bicyclo(2.2.2)octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a decahydronaphthalene-2,6-diyl group, a hydrogen atom contained in any of the groups (d), (e), and (f) may be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom, 
         L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 , and L 38  each independently represent a single bond, —COO—, —OCO—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or —C≡C—, when a plurality of M 32 s, M 34 s, M 35 s, M 37 s, M 38 s, L 31 s, L 33 s, L 35 s, L 36 s, and/or L 38 s are present, they may be the same or different, 
         X 31 , X 32 , X 33 , X 34 , X 35 , X 36 , and X 37  each independently represent a hydrogen atom or a fluorine atom, 
         Y 31 , Y 32 , and Y 33  each independently represent a fluorine atom, a chlorine atom, a cyano group, a thiocyanate group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a difluoromethoxy group, 
         p, q, r, s, and t each independently represent 0, 1, or 2, but q+r and s+t are each 2 or less), 
         or at least one compound selected from the group consisting of compounds represented by general formulae (IVa), (IVb), and (IVc): 
       
       
         
           
           
               
               
           
         
         (wherein R 41 , R 42 , R 43 , R 44 , R 45 , and R 46  each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, one methylene group or two or more non-adjacent methylene groups in the alkyl group or the alkenyl group may each be substituted with —O— or —S—, and one or more hydrogen atoms in the alkyl group or the alkenyl group may each be substituted with a fluorine atom or a chlorine atom, 
         M 41 , M 42 , M 43 , M 44 , M 45 , M 46 , M 47 , M 48 , and M 49  each independently represent a group selected from the groups consisting of 
         (g) a trans-1,4-cyclohexylene group (where one methylene group or two or more non-adjacent methylene groups in the trans-1,4-cyclohexylene group may each be substituted with —O— or —S—), 
         (h) a 1,4-phenylene group (where one —CH═ group or two or more non-adjacent —CH═ groups in the 1,4-phenylene group may each be substituted with a nitrogen atom), and 
         (i) a 1,4-cyclohexenylene group, a 1,4-bicyclo(2.2.2)octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a decahydronaphthalene-2,6-diyl group, a hydrogen atom contained in any of these groups (g), (h), and (i) may be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom, 
         L 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 , and L 49  each independently represent a single bond, —COO—, —OCO—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or —C≡C—, when a plurality of M 42 s, M 43 s, M 45 s, M 46 s, M 48 s, M 49 s, L 41 s, L 43 s, L 44 s, L 46 s, M 47 s and/or L 49 s are present, they may be the same or different, 
         X 41  and X 42  each independently represent a trifluoromethyl group, a trifluoromethoxy group, or a fluorine atom, X 43 , X 44 , X 45 , X 46 , X 47  and X 48  each independently represent a hydrogen atom, a trifluoromethyl group, a trifluoromethoxy group, or a fluorine atom, however, at least one of X 41  and X 42  represents a fluorine atom, one of X 43 , X 44 , and X 45  represents a fluorine atom, one of X 46 , X 47 , and X 48  represents a fluorine atom, X 46  and X 47  do not represent fluorine atoms at the same time, and X 46  and X 48  do not represent fluorine atoms at the same time, 
         G represents a methylene group or —O—, 
         u, v, w, x, y, and z each independently represent 0, 1, or 2, but u+v, w+x, and y+z are each 2 or less). 
       
     
     
       2. The polymerizable-compound-containing liquid crystal composition according to  claim 1 , wherein when Z 11  in general formula (I) is —S 12 —R 12 , least one of S 11  and S 12  represents an alkylene group having 2 to 12 carbon atoms where a methylene group in the alkylene group may be substituted with an oxygen atom, —COO—, —OCO—, or —OCOO— as long as oxygen atoms are not directly bonded to each other. 
     
     
       3. The polymerizable-compound-containing liquid crystal composition according to  claim 1 , wherein R 11  and R 12  in general formula (I) each independently represent formula (R-1) or (R-2). 
     
     
       4. The polymerizable-compound-containing liquid crystal composition according to  claim 1 , wherein the liquid crystal composition is used in a liquid crystal display element including a pair of substrates, a liquid crystal interposed between the substrates, a transparent electrode, and a polarizer, in which a liquid crystal alignment capability is provided by polymerizing a polymerizable compound contained in the liquid crystal composition. 
     
     
       5. The polymerizable-compound-containing liquid crystal composition according to  claim 1 , wherein the liquid crystal composition contains 0.01% to 2% by mass of the at least one compound selected from the polymerizable compounds represented by general formula (I), 5% to 70% by mass of the at least one compound selected from the compounds represented by general formula (II), and 5% to 70% by mass of the at least one compound selected from the group consisting of the compounds represented by general formulae (IIIa), (IIIb), and (IIIc) or the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       6. The polymerizable-compound-containing liquid crystal composition according to  claim 1 , wherein the liquid crystal composition contains, as the third component, at least one compound selected from the group consisting of the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       7. A liquid crystal display element comprising:
 the polymerizable-compound-containing liquid crystal composition according to  claim 1 , 
 wherein a liquid crystal alignment capability is provided by polymerizing the polymerizable compound contained in the polymerizable-compound-containing liquid crystal composition. 
 
     
     
       8. The liquid crystal display element according to  claim 7 , wherein a dielectric anisotropy of the polymerizable-compound-containing liquid crystal composition is negative. 
     
     
       9. The polymerizable-compound-containing liquid crystal composition according to  claim 2 , wherein R 11  and R 12  in general formula (I) each independently represent formula (R-1) or (R-2). 
     
     
       10. The polymerizable-compound-containing liquid crystal composition according to  claim 2 , wherein the liquid crystal composition is used in a liquid crystal display element including a pair of substrates, a liquid crystal interposed between the substrates, a transparent electrode, and a polarizer, in which a liquid crystal alignment capability is provided by polymerizing a polymerizable compound contained in the liquid crystal composition. 
     
     
       11. The polymerizable-compound-containing liquid crystal composition according to  claim 3 , wherein the liquid crystal composition is used in a liquid crystal display element including a pair of substrates, a liquid crystal interposed between the substrates, a transparent electrode, and a polarizer, in which a liquid crystal alignment capability is provided by polymerizing a polymerizable compound contained in the liquid crystal composition. 
     
     
       12. The polymerizable-compound-containing liquid crystal composition according to  claim 2 , wherein the liquid crystal composition contains 0.01% to 2% by mass of the at least one compound selected from the polymerizable compounds represented by general formula (I), 5% to 70% by mass of the at least one compound selected from the compounds represented by general formula (II), and 5% to 70% by mass of the at least one compound selected from the group consisting of the compounds represented by general formulae (IIIa), (IIIb), and (IIIc) or the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       13. The polymerizable-compound-containing liquid crystal composition according to  claim 3 , wherein the liquid crystal composition contains 0.01% to 2% by mass of the at least one compound selected from the polymerizable compounds represented by general formula (I), 5% to 70% by mass of the at least one compound selected from the compounds represented by general formula (II), and 5% to 70% by mass of the at least one compound selected from the group consisting of the compounds represented by general formulae (IIIa), (IIIb), and (IIIc) or the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       14. The polymerizable-compound-containing liquid crystal composition according to  claim 4 , wherein the liquid crystal composition contains 0.01% to 2% by mass of the at least one compound selected from the polymerizable compounds represented by general formula (I), 5% to 70% by mass of the at least one compound selected from the compounds represented by general formula (II), and 5% to 70% by mass of the at least one compound selected from the group consisting of the compounds represented by general formulae (IIIa), (IIIb), and (IIIc) or the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       15. The polymerizable-compound-containing liquid crystal composition according to  claim 2 , wherein the liquid crystal composition contains, as the third component, at least one compound selected from the group consisting of the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       16. The polymerizable-compound-containing liquid crystal composition according to  claim 3 , wherein the liquid crystal composition contains, as the third component, at least one compound selected from the group consisting of the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       17. The polymerizable-compound-containing liquid crystal composition according to  claim 4 , wherein the liquid crystal composition contains, as the third component, at least one compound selected from the group consisting of the compounds represented by general formulae (IVa), (IVb), and (IVc). 
     
     
       18. A liquid crystal display element comprising:
 the polymerizable-compound-containing liquid crystal composition according to  claim 2 , 
 wherein a liquid crystal alignment capability is provided by polymerizing the polymerizable compound contained in the polymerizable-compound-containing liquid crystal composition. 
 
     
     
       19. A liquid crystal display element comprising:
 the polymerizable-compound-containing liquid crystal composition according to  claim 3 , 
 wherein a liquid crystal alignment capability is provided by polymerizing the polymerizable compound contained in the polymerizable-compound-containing liquid crystal composition. 
 
     
     
       20. A liquid crystal display element comprising:
 the polymerizable-compound-containing liquid crystal composition according to  claim 4 , 
 wherein a liquid crystal alignment capability is provided by polymerizing the polymerizable compound contained in the polymerizable-compound-containing liquid crystal composition.